Milwaukee’s East Side is changing. Though the historic neighborhood is becoming cluttered with cookie cutter apartment complexes, rent is on the rise, and chain restaurants continue to move it, a few businesses remain to serve as vestiges of the East Side many have come to know and love. One such business is Pizza Shuttle, which has stood prominently on Farwell Avenue for nearly three decades as a go-to late night haunt, a trusted place to grab a slice before (of after) heading to Brady Street, and a pizzeria with a shockingly vast delivery area. For those reasons and more, it’s nothing short of an iconic Milwaukee establishment. Another thing Pizza Shuttle is known for, at least until recent years, is being the home to what’s been called “Wisconsin’s Largest Pizza Challenge.”

The since-discontinued challenge tasks two participants with taking down a 12-pound, 28-inch diameter hand-tossed pizza (which is still available for purchase on the menu) in just 45 minutes, without being able to leave the table or drink more than a single cup of water. Those who have the intestinal fortitude to finish this imposing pizza in the allotted time take home $500 and, perhaps more valuable, glory. Wanting a chance at the distinction of doing something only a select few people have done (and a bunch of free Pizza Shuttle), Milwaukee Record co-founders/editors Tyler Maas and Matt Wild, and Director of Advertising Josh Hoppert tried, then absolutely failed, Wisconsin’s Largest Pizza Challenge.

Tyler Maas: A few months ago, I reached out to Packers great and former Burger King sandwich namesake Gilbert Brown through a mutual friend to see if he’d join me in attempting to take down this monster ‘za. He never got back to me. Real cool, Gravedigger. Thus, I was forced to enlist my co-workers for an eating endeavor I had exactly zero faith we’d accomplish. I arrive first, place our order (pepperoni and sausage, per the request of my mushroom-and olive-averse partners), and ask owner Mark Gold—who approved our unorthodox three-man attempt, no doubt after seeing what Matt Wild looked like—some things about the challenge. He’s surprised I even recall its existence, but seems happy to recount past attempts that ranged from grown men moaning face-down on the floor and one set of traveling competitive eaters who dispatched the entire pie in 15 minutes. Gold estimates eight teams have conquered the 12-pound pizza in the contest’s history. We won’t be the ninth.

Matt Wild: I walk to Pizza Shuttle from my apartment—a brisk 15-minute jaunt—feeling good about myself, feeling good about my body. I’m relatively healthy, relatively in the prime of my life. I weigh 140 pounds soaking wet. My skin is okay. I’m happy. All this will change in about 90 minutes.

Josh Hoppert: I feel like The Mighty Ducks‘ Fulton Reed when I show up to Pizza Shuttle Monday morning. Powerful, but lacking the skills and experience needed to excel in the Game of Eat. A puncher; not yet a boxer. Would my years spent training with my grandfather at Sheboygan’s many Chinese buffets translate to a team takedown of a 12-pound monster? Probably not.

TM: We nervously pace around the restaurant as it begins to fill up on its lunch hour. To keep my stomach expanded, I keep drinking water, the only thing I’ve ingested since taking down a medium vegetarian pizza myself the night before to “train.” Meanwhile, Mr. Gold breaks down what we’re about to put inside our bodies: about three pounds of dough, nigh upon four pounds of fresh Wisconsin mozzarella, a pound of ground sausage from Chicago, and “a couple hundred” slices of pepperoni. My mouth is watering and my teeth are chattering at the same time.

MW: We’re joined today by Pizza Shuttle’s social media team, Armando and Katie. They’re both young, chipper, friendly, and fun, and they seem shockingly unfazed about the prospect of spending the next hour with a trio of schlubs attempting to ingest an unholy amount of pizza. They post a few pictures on Facebook and Instagram of us sizing up the pie, tweet about our impending challenge on Twitter, and do something or other on Snapchat. For the next hour I ponder who has the stranger job: us or them.

JH: A few minutes before 11:30 a.m., the biggest pizza I have ever seen lands on our table. Patrons gather ’round and my confidence actually skyrockets. I really think we can do this. I’ve taken a two-pound pizza to the head on multiple occasions, so taking down four-plus pounds really sounds doable. Ring the bell, Apollo.

TM: Jesus Christ. This pizza is big. And I know a thing or two about big pizzas. With all due respect to Zaffiro’s, this pizza looks even better…and bigger. Josh and Matt say quasi-positive things about our chances. Rookies. I remain confident that 1. I’ll eat the most of our trio, and 2. We’ll come nowhere close to finishing this.

MW: The giant pizza causes a small scene, as giant pizzas tend to do. Fellow diners stare at it, and us, with looks somewhere between disbelief and disgust. One dude just shakes his head and walks out the door. This open contempt only emboldens me. What’s more, I like Pizza Shuttle pizza, have always liked Pizza Shuttle pizza. It’s one of those Milwaukee staples that’s a Milwaukee staple for a reason. The table-sized ‘za looks delicious. Let’s do this.

JH: We let the giant pie cool to a comfortable temperature and get moving at 11:31 a.m. CST. Tyler recommends that we all eat as fast as possible for the first 15-ish minutes, before our stomachs start sending pain signals to our brains. Good advice, but as evidenced by my extended exchange of mid-meal Stand By Me quotes with Matt, this would be more about fun than actually winning. Plus, the pizza tastes great (especially for something that big), so it’s hard not to savor it a little.

MW: Yeah, I’m trying to keep things light by joking around, laughing about that Lardass scene in Stand By Me (“The Women’s Auxiliary barfed all over the Benevolent Order of Antelopes!”), and trying to make small talk with Armando and Katie. Seven or eight pieces in, it dawns on me that this is more than I typically eat in an entire week. In fact, I’ve been forgetting to eat lately. I’ve taken to setting alarms on my phone reminding me to put food in mouth. It’s weird that this his happening now, as I recently finished a book—Christopher J. Yates’ delightfully twisty Black Chalk—where the same thing happens to the main character. Man, what a strange and confounding book. The part where Jolyon convinces Mark to follow him to the top of Loser’s Leap and…wait. Must keep eating. Must keep eating…

TM: Despite my sage warning to eat as quickly as possible to get ahead of the brain’s inevitable signal to “STOP!” that arrives around the 15-minute mark, these fuckers are dicking around. As these newbs waste precious time trading quotes from overrated ’80s films, I keep my head down (both focused and ashamed) and quickly plow through two rows of the pizza. Fifteen pieces in as many minutes. The pizza is really good, especially the cheesy and sauce-laden middle squares. But I know this will soon become a taxing ordeal, no matter how good the pizza tastes. Matt’s phone rings and he answers it! It’s almost like he’s not taking this self-assigned task to eat a 12-pound pizza on a Monday seriously. It’s his wife, asking why he’s doing this. That’s the reason why I’m not married, folks. Well, that and routinely doing things like this has rendered me an impossibly depressed and wholly unlovable foodbag. Mostly the second part, I suppose.

JH: Fifteen minutes in and Tyler was right. The pace has slowed a lot as we all start to fill up and the pizza has further cooled. We’re a one-third or so in and I’ve eaten all the outer edge pieces within my reach, figuring the topping-heavy inner pieces would keep things more lively later in the game. We’ll see.

MW: Something called The Chew is on TV, which features people smiling and eating. We’re no longer doing the first part.

JH: Halfway through the hour and roughly halfway through the pizza. Lively isn’t a word we use anymore. Still eating, but more slowly. Still joking around, sort of. Still fun. Sort of. Matt sets some team goals. “Love Is A Battlefield” starts playing and nobody can confirm my claim that 30 Rock‘s Tracy Jordan once sang it at a strip club. Deep breaths. Small bites. Is it too late to retake my AP Physics exam? Sort of.

MW: My mind drifts back to a decade ago, when I foolishly challenged my then-roommate, Sam, to a brat eating contest at my family’s fishing cabin. Sam had a good six inches and 60 pounds on me, and he absolutely destroyed me. While I struggled to finish brat number four—shirtless, crumpled over in pain, my friend Kelly consoling me with whiskey and inspirational quotes—Sam popped the things like they were goddamn candy, occasionally taking time out to catch a fucking fish. What was I thinking back then? What am I thinking now?

TM: By this point, my eating pace—no doubt matching the pace of my marinara-tinged blood slogging through my veins—has slowed. The team’s anchor is dragging. My partners are doing no better. Wishing to look anywhere that isn’t the pizza I was eagerly masticating half an hour earlier, I gaze upward and see a partially inflated Mylar balloon, likely left from a child’s birthday party. I think of that faceless child, how he or she has their whole life ahead of them, and a chance to avoid the same mistakes I’ve made to bring me to the very same table where they’d celebrated just days earlier. I look to my right and notice the Frogger on the side of the arcade machine is wearing a necktie and a watch. Meanwhile, I’m technically at work in a sauce-stained Masked Intruder T-shirt. I wonder if Frogger’s company is hiring. I know the commute is a nightmare, but it still seems like an upgrade at the moment.

JH: Forty-five minutes in. Food drunk, edgy, a little sad. We’re something like two-thirds done, but there might as well be 12 more pizzas on the way. No sympathy for us poor devils as the Grateful Dead’s “St. Stephen” starts to play. Tyler’s not a huge fan. Ordinarily, I’d fire back with, “At least it’s not the Ungrateful Undead,” but this is no time for jokes. Will it ever be again? I grab the biggest piece left on the table and get to slow, angry work.

MW: Things start to fall apart. I’m sweating profusely, wondering why I chose to wear my nice pants to such a greasy endeavor. The room starts to fade in and out, contract and expand. I’m already mentally canceling plans for the rest of the day. I begin to confuse Armando and Katie for similar-looking people I know: Armando for my friend Bobby; Katie for another friend’s wife, also named Katie. “Number 44!” comes the call over Pizza Shuttle’s P.A. I try to put myself in the shoes of this mythic Number 44. He or she is hungry, expectant, happy, unburdened by the gastrointestinal slings and arrows of Wisconsin’s Largest Pizza Challenge. I am not this person. I will never be this person again. Despair.

TM: Realizing I’ve chewed the same bird-sized bite of my, like, 22nd slice over 60 times, I set down the half-square and call it a day with a few minutes remaining. I’d say we gave it a hell of a try, but we didn’t. Next time I do one of these, I’m bringing Gilbert Brown…or John Jurkovic at the very least. Like an hour before, I’m on my feet again, pacing nervous and unsure of what’s about to happen to me. I’m taking a strange solace in Josh and Matt looking miserable. Welcome to the jungle, boys. Thanks again for the shot at glory, Pizza Shuttle.

JH: 12:31 p.m. Half of that big slice I grabbed is still left, along with about 17 more uneaten slices. I box up what remains to take home. When I start eating again in about 11 years, the two boxes of leftovers should feed me and my extended family for three-to-five days. You win, Pizza Shuttle.

MW: The final song we hear as we drag ourselves out of Pizza Shuttle and back into the real world? Bob Marley’s “Three Little Birds.” “Don’t worry, about a thing / ‘Cause every little thing, gonna be alright,” Marley sings. I’m not so sure about that Bob, but I appreciate the optimism.